How I Hired My First Assistant: Lessons Learned and a Simple Manual for Success

When I hired my first assistant, I was excited. I imagined the relief of having someone to share the workload, the freedom to focus on what truly mattered, and the extra time I’d gain. But in reality, it didn’t start out that way. I made mistakes – plenty of them. Looking back now, I realized how much I had to learn, and I want to share that with you so you can avoid the same pitfalls.

The Beginning: Excitement Meets Chaos

At first, I didn’t know what to do with my assistant. Sure, I had a long to-do list, but when it came to actually assigning tasks, I froze. I ended up creating tasks just to keep her busy, rather than letting her handle real responsibilities that could have freed up my time. I was hesitant to let go of control, afraid she wouldn’t do things “my way.”

But then, something surprising happened. My assistant called me out. She said, “I can do more. Let me take things off your plate.” Her confidence and honesty made me realize how much I was holding her back – and myself, too. That conversation changed everything.

What Should an Assistant Do for a Multi-Business Owner?

If you’re juggling multiple businesses, the value of a skilled assistant is immeasurable. But first, you need to know what to delegate. Here’s a simple guide:

• Administrative Tasks: Managing emails, scheduling meetings, handling travel arrangements—these are the basics.
• Project Coordination: Tracking progress, maintaining timelines, and ensuring smooth communication with stakeholders.
• Personal Tasks: Reminders for personal errands, booking appointments, or even ordering gifts for special occasions.
• Business-Specific Tasks: Depending on your industry, this might include market research, social media updates, or preparing reports.

The key is to align tasks with both your needs and your assistant’s strengths. A good assistant isn’t just an extra pair of hands—they’re a partner in your productivity.

Best Strategies for Working with an Assistant

Here’s what I’ve learned works best:

1. Define Roles Clearly: Start with a detailed job description. Be clear about expectations and revisit them regularly as your needs evolve.
2. Set Priorities: Use task management tools to align on daily, weekly, and monthly goals. It keeps both of you on track.
3. Empower Them: Trust your assistant to make decisions within defined boundaries. This not only boosts their confidence but also reduces the back-and-forth.
4. Feedback is Everything: Schedule regular check-ins to discuss what’s working and what isn’t. This keeps communication open and strengthens your working relationship.

For example, I learned to hand over my email inbox. At first, it felt like losing a lifeline, but it gave me back hours of focus every day.

Mistakes to Avoid

Here are some lessons from my experience:

• Micromanaging: Trust is critical. Constantly checking up on tasks wastes everyone’s time.
• Assigning Busywork: Your assistant is there to create value, not just tick boxes.
• Unclear Instructions: Be specific about what you need and when you need it.
• Overloading Them: Remember, an assistant is human too. Don’t pile on everything you don’t want to do.

Once, I overloaded my assistant with too many tasks at once. The result? Missed deadlines and unnecessary stress for both of us. I learned that clear priorities and manageable workloads are non-negotiable.

Examples of Effective Assistant Utilization

To help you see the potential, here are a few examples:

• Scheduling Overlaps: My assistant once coordinated meetings for three businesses without a single conflict.
• Content Prep: She organized blog drafts and managed my social media schedule.
• Market Research: When launching a new product, she gathered data that saved me hours of time.

These tasks might seem simple, but they’re transformative when done well.

Conclusion: Learning and Growing Together

Hiring an assistant isn’t just about delegating tasks; it’s about building a partnership. My first assistant taught me as much as I taught her, and the experience reshaped how I approach leadership and delegation.

If you’re a multi-business owner, having the right assistant can be a game-changer. But it requires clear roles, open communication, and trust. These are the same principles we dive into during my 12-week coaching program, where we cover not only how to hire and manage your assistant but also how to optimize your time and focus on what truly matters.

Your assistant isn’t just someone who works for you; they’re someone who helps you work better. Let them.